Hydrochloric Acid → HCID 58558036, compound

HRID 1969790Notes

Reaction equation

HRID 1969790 reaction equation
[C:1]1([N:13]2[CH2:17][CH2:16][CH:15]([NH:18]C(=O)OC(C)(C)C)[CH2:14]2)[N:5]2[C:6]3[CH:12]=[CH:11][NH:10][C:7]=3[N:8]=[CH:9][C:4]2=[CH:3][N:2]=1.Cl.CCN(C(C)C)C(C)C.[CH:36]1([S:39](Cl)(=[O:41])=[O:40])[CH2:38][CH2:37]1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:1]1([N:13]2[CH2:17][CH2:16][CH:15]([NH:18][S:39]([CH:36]3[CH2:38][CH2:37]3)(=[O:41])=[O:40])[CH2:14]2)[N:5]2[C:6]3[CH:12]=[CH:11][NH:10][C:7]=3[N:8]=[CH:9][C:4]2=[CH:3][N:2]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2760919Cyclopropanesulfonyl chloride2×HCID 67998679HCID 67998679, compound

Product 1

HCID 58558036HCID 58558036, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 1-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)pyrrolidin-3-ylcarbamate (0.175 g, 0.511 mmol, Example #D.1.42) in DCM (10 mL) was added HCl (4 N in 1,4-dioxane, 1.28 mL, 5.11 mmol). After about 4 h at ambient temperature, the reaction mixture was concd in vacuo. The residue was suspended in DCM (10 mL) and DIEA (0.446 mL, 2.56 mmol) was added to the reaction mixture resulting in a nearly homogeneous mixture. To the mixture was added cyclopropanesulfonyl chloride (0.079 g, 0.56 mmol). After about 2 h at ambient temperature, additional cyclopropane-sulfonyl chloride (0.079 g, 0.56 mmol) was added. After about 6 h at ambient temperature, saturated aqueous NaHCO3 (10 mL) was added to the reaction mixture. The organic layer was separated and the aqueous layer was extracted with DCM (3×10 mL). The combined organic layers were concd in vacuo and purified by chromatography on silica gel (40 g) eluting with 50-90% MeCN in DCM to provide N-(1-(6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-1-yl)pyrrolidin-3-yl)cyclopropane-sulfonamide (0.125 g, 70%) as a tan solid: LC/MS (Table 1, Method a) Rt=1.42 min; MS m/z: 347 (M+H)+.

Workup

  1. customresulting in a nearly homogeneous mixture
  2. waitAfter about 2 h at ambient temperature
  3. waitAfter about 6 h at ambient temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with DCM (3×10 mL)
  6. custompurified by chromatography on silica gel (40 g)
  7. washeluting with 50-90% MeCN in DCM

Sources & evidence

ORD record
ord-9acb88ca9ca34cd29f559e93429e6721
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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